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 Preparing for Sales 

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Michael Santos

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Preparing for Professional Sales from Prison


Scott learned a simple sales lesson as a young man: People don’t want to be sold, but they love to buy; a successful salesperson learns what their customer values. Scott’s entrepreneurial mindset and his willingness to invest in personal development led to a successful sales career in both business-to-consumer and business-to-business sales. Scott credits his reading, vocabulary, and arithmetic skills with his success today. He found that some of the lessons taught in school taught Scott to “learn how to learn.” He believes in the value of exercising the mind by continually learning new things, even if they’re not necessarily rewarded by profits.


  • In Scott’s story, participants in prison will learn the importance of developing excellent communication and critical thinking skills, embracing delayed gratification, and planting the seeds of success today. An individual in one situation can always focus on personal development as a strategy to open new opportunities.

Lesson Requirements:

  • Watch the video that accompanies the lesson
  • Write a definition of each word highlighted in bold and written in italics
  • Choose ten of the vocabulary words and write one sentence for each word.  
  • Respond to a minimum of three open-ended questions by following instructions at the end of the lesson.

Lesson Outcome:

  • Participants will increase their vocabulary by at least ten words.
  • Participants will improve writing skills and their ability to contemplate how their responses to open-ended questions relate to their prospects for success upon release.
  • Participants will add to their journal, demonstrating a self-directed, self-improvement pathway to prepare for success upon release.

Our entire team at Prison Professors expresses gratitude to Scott for sharing his professional sales expertise with us. Scott demonstrated that individual goal setting and patience will pay long-term dividends. Scott serves as a role model we can learn from in preparation for overcoming the career challenges most people encounter upon leaving prison. 

Scott’s Background:

Throughout his childhood and teen years, Scott enjoyed school; yet he felt challenged by a lack of freedom. Although not particularly interested in all of his classes, some subjects inspired him than others. It took years for Scott to discover that being in school was about learning how to learn, and learning how to use and exercise his mind.

The importance of good grades pushed Scott to work hard. He started as B+ student, with the usual middle- and high-school distractions of friends, sports, and wanting to have fun. As he matured through school, he developed a greater appreciation for the importance of learning. Inspired by fellow classmates who earned As and A+ grades, Scott embraced an “if they can do it, I can do it” mindset that kicked his learning into high gear. His grades improved.

After high school, Scott studied general business management with a certificate in entrepreneurship at University of Iowa. Scott earned what he described as a vague degree, meaning he graduated without an exact career pathway, such as engineering or other more specific careers. Finding direction required self-reflection as he determined his next steps and path forward.


I was a terrible student in my youth. My lack of interest in school was the result of a bad philosophy—I didn’t appreciate education. I enjoyed playing sports and admired great players, but I was a mediocre athlete.

Coaches teach that exceptional athletes translate their skillsets into other sports from a developed athletic intelligence. That high level of competency translates to other sports.

In prison, I learned to appreciate education and the importance of developing fundamental skills. As with sports, in education the knowledge developed in one area translates to other areas. Foundational knowledge supports the development of critical thinking—a skill that is continuously emphasized in our courses.

First jobs:

Scott’s first experience with sales came at an early age. While shopping at Sam’s Club with his parents, he noticed a box of Slim Jim’s beef sticks cost Sam’s Club $.25 per piece. He saw Sam’s Club selling the same beef sticks for $1.25 per piece to customers. Realizing he could sell the beef sticks at his school, Scott purchased a box and resold them at a profit during school lunchtime. He enjoyed the rush of the sale and the impact the extra money had on his life. The experience inspired Scott’s interest in sales as a career.

During high school and college, Scott worked as a busboy, server, and bartender in the restaurant and hospitality industry. By regularly interacting with many different customers, he became quite comfortable with the idea of sales and his ability to communicate effectively and professionally.

Scott indicates all of these increased work opportunities had a tremendous impact on his communication skills, vocabulary skills, critical thinking skills and taught him the value of hard work. He also learned how being a good salesman as a waiter and bartender lead to increased tips.

Early Career, Role Models, and Inspiration.

After graduating from college, Scott took a job selling mini blinds. The company advertised on television commercials, with flyers, on the radio, and in newspapers. Inbound calls from interested customers were assigned to sales reps. Scott also found his own leads by going door-to-door in new housing developments, selling to homeowners that were interested in blinds for their new homes. That experience brought with it the freedom of self-direction. His primary responsibility was making sure customers that purchased were satisfied with the product. He nurtured leads, set appointments, went to customers’ homes and measured windows, and presented customers with options. He earned a small salary plus a commission based on his sales.


Scott brought up several important data points that were foreign to me when I entered prison, but I learned and mastered them during my 26 years inside.

  1. The building blocks to the sales process for Scott required him to first get leads.
  2. A foundational level of math and algebra skills were necessary in Scott’s job because he needed the skillset to compute the correct window measurements and calculate the amount of materials needed for the order. Scott said he did not really value the importance of math classes while he was in school, but in his real-life work environment that knowledge was invaluable.
  3. The combination of critical thinking skills and vocabulary work together. According to Scott, no matter what you’re selling, you become more successful by being more persuasive. Intellectual athleticism is the ability to use language effectively: putting words into sentences and sentences into paragraphs. Such verbal fluency comes from investing the time to develop and expand one’s vocabulary.  

Scott believes that intellectual, professional, and personal development are inextricably intertwined. When people develop some level of expertise in one area, this aids in developing the art of critical thinking. We can visualize a good analogy for Scott’s belief by comparing business to sports. Athletes who excel at one sport typically excel at other sports. The skills and competencies are mostly transferrable from one sport to another. In business, proper communication and critical thinking skills are not only transferrable from one industry to another but are an essential requirement for employment in every industry.

While Scott knew his likes and dislikes from a young age, not everyone else has the same clarity. For some folks, introspection takes time. Each individual grows, matures, and learns at a different pace. There is nothing wrong with learning about oneself later in life. People who learn from Scott can see that moving forward to success becomes more manageable once we learn about ourselves.

  • How did Scott’s first experience with sales in school impact his career goals?
  • What feelings did you have when experiencing your first taste of success?
  • How can you position yourself to experience success once again?
  • In what ways did Scott’s mindset of being restricted at school resemble the challenges you faced?
  • In what ways can Scott’s strategies help you succeed in the future?

Scott’s Steps Toward Successful Sales:

Scott learned the nuances of cold leads, warm leads, hot leads, and qualified leads:

  • Cold Leads – A customer who has no idea what you want until you speak. Cold leads are also known as cold calls and door-to-door sales.
  • Warm Leads – A customer who has an interest in the product and may make a purchase. A warm lead is also a qualified lead.
  • Hot Leads – A customer who is ready to buy, wants to buy, and has an immediate need for the product. A hot lead is also a qualified lead.

A sales professional must learn how to communicate with each different type of lead. Mastering communication has a fantastic influence on a sales professional’s success. A successful salesperson learns what their customer values. The sales professional must be able to communicate effectively in order to persuade the customer to reveal their reasons for buying–not what the sales person thinks is the reason.


While in prison, individuals can learn the necessary building blocks for success in professional sales. People in jails and prisons may not be able to knock on doors or makes sales calls, but they can begin developing the skills they’ll need when they return to society and seek employment. Think now about how your language will communicate differently to different people. Think about “what’s in it for me?”

Scott left his position with the blinds company for a job in solar sales and installations, an industry with many ups and downs. After a couple of years in that job, he aspired to change from business-to-consumer sales into business-to-business sales. The difference between those two vertical markets has advantages and disadvantages.

  • Business-to-consumer (B2C) sales is a straightforward process between sales and the consumer. Basic skillset, or building blocks, for this kind of sales includes the art of listening. Sales is not about talking. The customer will say what they want if you listen. People don’t like to be sold, but they love to buy. Sales tend to lead to more sales due to the volume of potential customers. Technically, every person in the United States could be a customer. The customer ultimately decides whether to move forward with the purchase. B2C sales tend to have a short sales cycle. An example of B2C sales includes purchasing sneakers from a sporting goods store.
  • Business-to-business (B2B) sales is complex, with more stakeholders, more red tape, more approvals required, and more liability. Basic skills include figuring out who are competitors and how they capture market share. Further, not every business in the United States is a potential client because businesses have differing needs. B2B sales have a long sales cycle because of the many variables to consider. An example of B2B sales includes a manufacturer like Nike convincing a sporting goods store to sell its shoes in its stores.

Scott’s first business-to-business sales opportunity occurred at age 27 through an industry contact he developed while learning about medical implant sales. Many people told him medical sales had a high barrier to entry, but Scott did not let this dissuade him. While he never aspired to go into medical sales and he had no medical background or science training, the challenge of dealing with well-educated professionals appealed to him. He liked the technical aspect of selling medical equipment, the income potential, healthcare as a growing industry, and he liked the idea of contributing to the potential for better patient outcomes.

Scott pursued his career in medical device sales with intention. He built a network by meeting people in the industry and asking questions. Eventually he’d connected with nearly 50 people, many of whom shared industry opportunities with him. Through networking, he found a course about medical sales in Colorado that cost $4000 plus the expense of meals and lodging for two weeks—a significant personal investment. Within one week after completing the course, Scott landed a position with a small salary and high commission potential.

To achieve professional success in medical sales, Scott pursued self-directed learning in order to enter the industry. He understood that developing relevant credentials would increase his chances for a higher income. Launching a career in medical sales required discipline to balance the accountability and flexibility that came with selling high caliber medical implant devices. He thrived on the mindset that, although not experienced in the beginning, he saw others who were successful and believed that if one person could achieve success, he could as well. It was the mindset he used in high school when he rose to the challenge of earning the same A+ grades his peers earned.


People in jails and prisons should apply a high level of critical thinking when deciding how to best use their time. They should position themselves for success on the other side. Communicating in the language of business demonstrates an understanding of return on investment. Learn how to develop leads, close deals, and create value by listening to professionals like those profiled in our videos and courses.

Making a personal investment often requires personal sacrifice. The investment is worth it in the long run, but the risk-reward ratio demands an assessment of every decision along the way. Start now by making an investment in yourself. Self-development opens new opportunities.

The professional sales concept of “eat what you kill” played a direct role in Scott transitioning from salaried employee into a 100% commission-based sales role. The change was nerve-racking because it required him to work hard for sales, every day, in order to earn compensation.

The consequence of no sales is no income. Someone motivated by security and stability may be risk-averse and choose the dependability of a salaried income; whereas another person may choose a more aggressive, self-reliant compensation based on their contributions. Regardless of the chosen path, both can bring success. As a salaried employee, Scott possessed an internal drive to succeed as good employee, but for him the personal reward for achieving sales came from his commission-only compensation.

The prospect for success has an inverse relationship. An exceptionally successful sales professional embraces delayed gratification. Companies hiring sales professionals may offer a low salary and high commission base—more reward for the sales person and less risk for the company. An annual salary of $50,000 translates to about $700 per week after taxes and expenses. Commissions paid based on the percentage of sales become lucrative when gross sales reach $100,000 or more.

Scott believes new salespeople should see sales with a long-term strategy in place. According to Scott, very few sales opportunities exist where newcomers immediately rise to the top. While newcomers may not have the network and industry contacts to achieve immediate success, Scott believes anyone with a passion for success can achieve their goals.

Anyone currently facing challenges and watching this video can learn the following sales concepts from Scott:

  • Leads (Hot, Warm, Cold discussed above).
  • Visit face-to-face with customers when possible (Superb communication skills required).
  • Tracking quantity of products (Math skills required); and
  • Discussing options with customers (critical thinking skills required).


Targeted educational tracks (engineering, architecture) are very specific, spredictable career paths. Scott pursued an entrepreneurial path based on his comfort with a level of risk—he was willing to sink or swim on his decisions. A person who takes control of their own future has an entrepreneurial mindset. They understand nothing in life is guaranteed. They understand that whether business owner or sales professional, it might not work—and that inner-voice is their driving motivation to work harder for success. 

Working as a waiter and bartender helped Scott with his communication and sales skills. Out of college, Scott experienced a steep learning curve. Once in a professional sales role, he learned immediate self-reliance skills since part of his salary depended on his ability to close a deal. This new skill of self-reliance proved motivating for Scott.

How do our fears of failure influence our decisions? How can we build on our skills of self-reliance to realize our dreams? How do our language and communication levels change depending on our audience? Consider the following:

  • What are you doing now to prepare for new opportunities?
  • What opportunities for self-reliance currently exist around you?
  • Identify a fellow person in prison that can help you develop new skills.
  • What can you read to learn skills that will help you after you’re released?
  • In what ways can fear of failure become a motivating factor in your life?

Achieving Success While Facing Obstacles:

Someone in jail or prison thinking of entering professional sales upon release should understand these concepts:

The job market is not always friendly to formerly incarcerated people, or people whose backgrounds look different from the marketplace. Think now and identify what kind of person you are. There is no judgment on whether someone prefers security and stability or entrepreneurship or self-directed path. We must be able to assess strengths, weaknesses, opportunities and threats (the SWOT analysis we discuss in Prison Professors courses). Look at the people around you in your environment and ask yourself:

  • Who will you learn from? The guy who wants to be king of the TV room, or a leader such as Scott who achieved personal and financial success by working hard and following a self-directed, deliberate path?
  • What motivates you?
  • What will the job market look like for you?
  • How will you overcome challenges in the job market?

Sales is an esoteric position. Every sales call is unique. An unpredictable element exists because the customer is always changing. Anyone considering a career in sales should understand an objective versus a subjective pathway. For example, a mechanic has an objective pathway—mechanical diagnostic tests determine whether an engine is working or not working.

Sales, or persuasion, is subjective. A sales professional utilizes body language, voice inflection, which stories to tell, and the ability to respond with confidence as tools. An individual can develop and strengthen those qualities. Strong critical thinking skills require an individual’s investment in developing vocabulary. That is why the lessons in our courses are relevant. Connect the dots between where you are right now and where you’ll be five years from now—every decision advances you closer to a successful outcome.

Through his years of experience in sales, Scott learned having an entrepreneurial mindset means becoming friendly with the word “No.” Scott strongly believes in the concept of delayed gratification – doing something today where you receive the reward sometime in the future. Sales is a long-term strategy, and not every sales call leads to a closed deal. A sales professional cannot judge performance based on every loss. When you get knocked down, get back up. You can’t control the number of closed deals, but you can control whether or not you show up and keep going. Don’t give up.

According to Scott, success in sales requires several professional tools. These tools include the ability to:

  1. Develop leads;
  2. Close deals; and
  3. Create (or learn how to obtain) products to sell.

Many sales skills are learned by listening to successful sales professionals like Scott. Further, Scott believes success in sales also requires several personal skills. These skills include the ability to:

  1. Demonstrate excellent communication skills;
  2. Persuade others to one’s point of view;
  3. Read and show positive body language; and
  4. Control the inflection of one’s voice.

People currently facing challenges in prison can develop all of these skills. In many of our Prison Professor lesson plans, successful businesspeople emphasize the importance of learning excellent communication and critical thinking skills.

Rebuilding after experiencing a challenge comes from learning from good role models and emulating their behavior. Surrounding oneself with positive thinkers who support improvement and forward momentum cannot be overstated.

Although difficult for many, overcoming a fear of failure is possible through hard work, goal setting, and determination. A person who strives for excellence will undoubtedly obtain success after their release. According to Scott, sales is similar to gardening. No matter how much water, fertilizer, and sun—you can’t rush it. Consistent care every day eventually results in a beautiful garden. Take small steps knowing that, in the future, the hard work and incremental steps will pay off.

Critical Thinking Questions:

  • Write at least three paragraphs, with a minimum of three sentences each, for each of the following questions.
  1. How did Scott’s early realization of his skillset aid in the development of his success?
  2. Have you realized your skillset, and how can it aid in your development?
  3. How does goal setting help you achieve success?
  4. Describe how independent learning about a career path can contribute to your success?
  5. Scott refused to let his fear of failure get in the way of his sales opportunities. How do your fears of failure impede your progress?
  6. Scott believes delayed gratification leads to success. Explain why you agree or disagree.
  7. Explain the difference between business-to-consumer and business-to-business sales.
  8. How can positive people influence your outlook in life?
  9. What does the following statement by Zig Ziglar mean to you: “If you can help other people get what they want, you can get everything that you want.”
  10. How does the development of strong communication skills help in your post-incarceration employment opportunities?

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